New York Yankees: Power Ranking the 10 Worst Trades in Team History

It's hard to argue with results. The Yankees have 27 world championships to their credit and they'll look to bring home No. 28 this season. But it's interesting to consider how many more titles they might have — if not for several bad trades throughout their storied history.

Every team has made the wrong move at one time or another, and hindsight is 20/20. Sometimes you trade that player that never showed any sort of promise, only to have him thrive with another team. Those deals hurt.

Then there are the times you'll trade for the veteran player, hoping they can recapture some magic, only to have them finish their career in mediocrity.

In their trade history, the Yankees have had a mixed bag of both.

Let's take a look at the 10 worst trades in their long and illustrious history.

February 5, 1942: Tommy Holmes for Buddy Hassett and Gene Moore

When the Yankees sent outfielder Tommy Holmes to the Boston Braves, Braves manager Casey Stengel felt that the Yankees were doing him a favor. In getting Hassett, the Yankees hoped they had finally found a bat to replace Lou Gehrig.

A bit naive on the Yankees' part; one does not replace Lou Gehrig.

At the time, the Yankees were drowning in outfield prospects and Holmes was expendable.

In 1941, Hassett hit .296 and owned a career .291 batting average up to that point. In today's game, with the use of advanced stats, this deal never happens. But in 1942, the Yankees had to have known this wasn't going to work out.

In his only full season with the Yankees, Hassett batted .284 with a .325 OBP, five home runs and 48 RBI. He was drafted into military service the following year and never played again.

As for Holmes, he played 11 seasons, 10 with the Braves. A two-time All-Star, Holmes retired with a career .302 batting average and finished in the Top 10 in batting average five times. In 1945, he became the only player to lead the league in home runs (28) and fewest strikeouts (9). He was also walked 70 times.

For those of you who love to point out all the instances of the Yankees trading away young players before they really get a chance to play, this is a great example. Even 50 years ago the Yankees were doing it.

October 21, 1981: Willie McGee to the St. Louis Cardinals for SP Bob Sykes

How bad was this trade? After coming to New York in 1981, Sykes never played another game in the major leagues.

McGee, who was the Yankees first round pick in the 1977 amateur draft, spent 13 of 18 seasons with the St. Louis Cardinals where he was a career .294 hitter.

He was an everyday player for the Cardinals team that won the World Series that year. In 1985, McGee won the NL MVP award and finished as a three-time Gold Glove winner and a four-time All-Star.

The Yankees so deeply regretted trading McGee that they tried multiple times to bring in players who could give them similar production, including Ken Griffey Sr. and Dave Collins. The Yankees basically tried to build an NL-style team all because of McGee, which didn't quite work out. They just didn't have the necessary pieces to play small ball.

May 16, 1976: Larry Gura to the Kansas City Royals for Fran Healy

In the 1950s, the Royals were basically the Yankees' farm system. The Yankees regularly pried talent from them for next to nothing, most notably Roger Maris.

In the deal that sent Gura to Kansas City for Healy, the Royals finally got a measure of revenge. Healy served mainly as a backup catcher to give Thurman Munson the occasional day off.

In two and a half seasons with the Yankees, Healy played in just 74 games and hit just .250 with no home runs and 16 RBI.

Gura, to his credit, pitched well in his first full season with New York in 1974, going 5-1 with a 2.41 ERA in eight starts. His only problem was having Billy Martin for a manager. Gura posted a 3.51 ERA the following season, but Martin wasn't a big Gura supporter.

After this trade, George Steinbrenner told Yankees manager, Lou Pinella, "Lou, I've won you the pennant. I got Steve Trout."

It didn't work out quite as well as Steinbrenner had exclaimed.

In 1986, Tewksberry was 9-5 with a 3.31 ERA. His minuscule 3.1 strikeouts and 9.9 hit averages through nine innings ensured the Yankee defense would get some work. Still his 2.1 walks through nine innings showed great control.

After landing with the Cubs, Tewksberry went 0-4 with a 6.75 ERA in two seasons. After that, he was sent to the St. Louis Cardinals, where he put up five straight seasons of above-average ERAs. In 1992, Tewksberry was very impressive, going 16-5 with a 2.16 ERA.

Trout was forgettable with the Yankees. He posted a 6.60 ERA in his only season in New York. He walked more batters (37) than he struck out (27).

Unfortunately for Mr. Steinbrenner, the Yankees did not win the pennant that season.

July 21, 1988: Jay Buhner to the Seattle Mariners for Ken Phelps

You've all seen the episode of Seinfeld that has made this trade so famous. When Frank Costanza asks George Steinbrenner, "How could you have traded Buhner for Ken Phelps?" most Yankee fans were asking themselves the same thing.

Phelps had a long swing and struck out a lot in the minor leagues, which kept him out of the majors until age 25. When he finally arrived, he put up very solid numbers. For whatever reason, Phelps would top out at 125 games played in 1986.

Steinbrenner loved Phelps. He had wanted to add his bat to the Yankee lineup so badly that when he finally got a chance, Phelps was almost 34 years old. In two years with the Yankees, Phelps would bat just .240 with 17 home runs.

Two years prior to this trade, the Yankees had basically stolen Buhner from the Pittsburgh Pirates for peanuts. But this trade destroyed that progress.

Buhner went on to play 14 seasons with the Mariners. He hit a total of 307 home runs for his career and ironically was a very similar player to Phelps in his prime, finishing his career with a .255 batting average.

Lowell was drafted in the 20th round by the Yankees in the 1995 MLB draft. They gave him just eight games in New York before they shipped him off to the Florida Marlins the following offseason. I think it's safe to say they pulled the trigger a bit too soon.

After coming to the Marlins, Lowell did have some health problems, but he quickly established himself as one of the elite third basemen in the game. Lowell drove in 85 runs or more in six of his seven seasons with the Marlins, eclipsing the 100 RBI mark twice.

Lowell batted .276 with 32 home runs and 105 RBI in 2003 when the Marlins won the World Series.

Of the players the Yankees received in exchange for Lowell, only Yarnall made it to the majors. He won one game.

One way of looking at this trade is that if the Yankees had kept Lowell, it's very possible there would be no Alex Rodriguez in the Bronx today.

When the Yankees acquired Marte and Nady for Jose Tabata, Jeff Karstens, Ross Ohlendorf and Dan McCutchen, the Yankees were getting a real deal.

At the time, the Yankees had an all-righty bullpen and were pitching well. Adding Marte gave them one of the top left-handed relievers in baseball. At the time of the trade, Marte was 4-0 with a 3.47 ERA.

Nady was batting .330 with 13 home runs and 57 RBI in 87 games for the Pirates when he came to the Bronx.

Despite his good numbers, Marte was terrible with the Yankees, posting a 5.40 ERA after the deal. Marte pitched for two more years with the Yankees, finishing with a 6.76 ERA, but he did strike out nearly a batter per inning.

Nady played pretty well for the Yankees, batting .268 with 12 home runs and 40 RBI in 59 games in 2008. Nady played in just nine games for the Yankees in 2009 before he suffered an injury which ended his season.

In terms of what the Yankees gave up, the Pirates certainly came out as the winner in this trade. Tabata, Karstens and Ohlendorf are all current starters on the Pirates. If the performance of the team after a trade makes a difference, then this trade is a wash, but to get three everyday starters in any trade is quite an accomplishment.

July 5, 2002: Ted Lilly to Oakland, Acquired Jeff Weaver from Detroit

This one is pretty bad. The Yankees sent Ted Lilly to Oakland, receiving Jeff Weaver in return in one of the worst trades in Yankee history. This is one of Brian Cashman's gems.

When the Yankees traded Lilly, he was 3-6 in 11 starts with a 3.40 ERA. With Weaver, they received a year and a half worth of mediocre starts. He would finish his time with the Yankees 12-12 with a 5.35 ERA over 32 starts and 15 relief appearances.

To his credit, Weaver had pitched on some bad teams prior to this trade and was certainly better than what he showed in New York. But having Ted Lilly would certainly have prevented some bad moves the Yankees made after this deal, such as the one for pitcher Jaret Wright in 2005.

Oh the Yankees of the 1980s. Gotta love 'em. Like so many of their trades that decade, this one falls under the "trading a prospect for an aging veteran to win now" category.

The worst loss in this trade was Fred McGriff, although he wouldn't reach his potential for a few years after this trade. The Yankees sent McGriff, along with Dave Collins and Mike Morgan to the Toronto Blue Jays for Dale Murray and Tom Dodd.

McGriff's career ended with 493 home runs, five All-Star games and an All-Star game MVP in 1994.

Murray pitched well in relief in 1982, posting a 3.16 ERA in a whopping 111 innings. But his ERA rose nearly a run and a half the following season and he was out of baseball soon afterwards.

July 30, 2004: Jose Contreras and Cash for Esteban Loaiza

The Yankees gave Contreras a $6 million signing bonus in 2002, second only to the $8.5 million they gave Hideki Irabu five years earlier. Foreshadowing, perhaps?

In his first season in the majors in 2003, Contreras looked like the real deal. In 18 games and nine starts, Contreras went 7-2 with a 3.30 ERA. He struck out 72 and allowed just 30 walks in 71 innings. Most impressively, he only gave up four home runs and posted a 1.15 WHIP while helping the Yankees into the postseason.

The following season, Contreras just couldn't keep the ball in the park. He allowed an ugly 22 home runs in 95.2 innings. For the most part, his numbers stayed almost the same, but his ERA ballooned to 5.64.

When the Yankees decided to give up and send Contreras to the White Sox for Esteban Loaiza, they should have known something was up because they were doing the same as Chicago was with Loaiza.

In 2003, Loaiza was 21-9 with a 2.90 ERA. He finished second in the AL Cy Young voting. In 2004, he made 21 starts for the White Sox, posting a 4.86 ERA and gave up more than a hit per inning.

Just like the Yankees with Contreras, the White Sox gave up on Loaiza and the two teams swapped players.

Loaiza made six starts for the Yankees and finished the season with a 8.50 ERA and a 2.05 WHIP. Contreras, on the other hand, pitched well after going to Chicago and was a big part of their 2005 World Series win.